Confined space entry/retrieval hoist and fall protection anchorage systems are known for lowering and raising a worker into and out of a confined space, such as a manhole, and for providing fall protection during the entry/retrieval and, at least in some applications, while the worker performs tasks in the confined space. Such systems typically have a mast/boom structure with two separate devices attached to the mast/boom structure for extending and retracting support lines that are attached to a worker suspended from the system, with one of the devices being a winch having a winch line supported by the mast/boom structure and connected to the worker for lowering and raising the worker into and out of the confined space, and the other device being a self-retracting lifeline (SRL) having another line supported by the mast/boom structure and attached to the worker for providing fall protection during the entry/retrieval of the worker and, at least in some instances, while the worker performs tasks in the confined space. Conventional systems mount the winch on the side of the mast/boom structure that faces away from the confined space/manhole and mount the SRL on the side of the mast/boom that faces the confined space/manhole. While conventional systems have proven suitable for their intended use, the location of the SRL on the side of the mast/boom structure facing the confined space/manhole increases the resultant load applied to the system, complicates the operation of the SRL, and increases the safety hazard because the SRL is typically mounted directly above the confined space/manhole due to the positioning of the mast/boom closely adjacent the confined space/manhole. Accordingly, there is room for improvement in a system that would address one or more of these issues.